Synthesis of 11-Keto Steroids

Chamberlin, E. M.; Ruyle, W. V.; Erickson, A. E.; Chemerda, J. M.; Aliminosa, L. M.; Erickson, Ralph Leroy; Sita, G. E.; Tishler, Max

doi:10.1021/ja01110a052

Cited by 18 publications

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“…or higher. This material, of about 95 to 100% purity, was found satisfactory in a use test for the preparation of A7-dehydrodiosgenin acetate (2). If diosgenin of still higher purity is desired, it can be prepared by crystallization from methyl ethyl ketone, ethyl alcoholacetic acid (1 to 1), or chloroformmethanol (1 to 1).…”

Section: Extraction and Purification Of Diosgeninmentioning

confidence: 97%

Isolation of Diosgenin by Acid Hydrolysis of Saponin

Rothrock¹,

Hammes²,

McAleer³

1957

Ind. Eng. Chem.

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Elimination of organic solvents in the initial extraction of the plant material, and utilization of hydrocarbon solvents with high selectivity for sapogenin, give a process that is simpler, less expensive, and more adaptable to large scale operations than classical processes EARLY in the commercial production of cortisone it was clearly evident that an alternative starting material was desirable to supplement the available supplies of bile acids. Therefore, a n intensive investigation was undertaken to find other steroids, especially of plant origin, that could be easily converted to cortisone. Among the genera of plants investigated were Strophanthus, Agave, Dioscorea, and Yucca, from which were derived sarmentogenin, hecogenin, and diosgenin, and yeasts from which ergosterol was obtained. This discussion deals with the process developed in these laboratories for the isolation of diosgenin (Ab-22a-spirosten-3/3-01) from Dioscorea tubers. Dioscorea barbasco amarillo, native to Guatemala, was selected as best of 65 investigated species of plants belonging to the family Dioscoreaceae from the standpoint of ready availability and yield of diosgenin.The classical methods of Tsukamoto and Ueno (77), Marker and others (6-9)) Wagner (72-75), and others (3, 5 ) available a t that time for the isolation of sapogenins were not commercially practical. In the isolation procedure employed most often by these investigators, the steroidal saponins were extracted by ethyl alcohol from ground plant material, then acid hydrolyzed to liberate the sapogenin from the glycoside. The crude sapogenins were obtained by the ether extraction of the hydrolyzate and were purified by being defatted with ligroin, treated with charcoal, and recrystallized several times. Often recrystallization through the acetate was required before pure sapogenin was obtained. A procedure for isolating diosgenin, somewhat similar to the one described here, is presented in a recent patent by Inoue and others (4).The process described involves direct acid hydrolysis of pulverized tuber, followed by preferential extraction of diosgenin from the dried hydrolyzate by hydrocarbon solvents, such as petroleum ether and heptane. The sapogenin can then be crystallized directly from the hydrocarbon solvent in a highly purified form. This simplified procedure is particularly suited to a species of tuber such as Dioscorea barbasco amarillo, containing only one sapogenin, because fractional crystallizations, chromatography, and other purification steps are eliminated in preparing a satisfactory product for further chemical work. An alternatite process by which saponin may be isolated, if desired, involves hot water extraction of sliced tuber. The aqueous solution thus obtained can be concentrated and extracted to yield saponin, or hydrolyzed and extracted to produce diosgenin. Isolation of Diosgenin From TubersThe process for the isolation of diosgenin from tubers consists of three major operations: preparation of the tubers, hydrolysis of the saponin, and extraction of the...

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